Detailed Itinerary

Day 1: September 25, 2027 – Arrival & Welcome to La Chiusa Private shuttle from Florence (~1.5 hours) to Hotel La Chiusa. Settle into your elegant suite with customizable climate control and sweeping views. Enjoy a warm welcome reception followed by a multi-course Tuscan dinner at Ristorante La Chiusa, featuring fresh garden ingredients and the estate’s own olive oil and wines. Accommodation: Hotel La Chiusa.

Day 2: September 26, 2027 – Montepulciano & Contucci Winery Delicious La Chiusa breakfast with fresh pastries, local cheeses, and inspiring views. We drive just 15 minutes to the iconic hilltop town of Montepulciano for a very special private wine tasting at Contucci Winery. Kent and Allison have known owner Andrea Contucci and his family for years, and he will personally guide us through the historic cellars—home to one of Tuscany’s most storied winemaking legacies dating back over a millennium (with roots in the 11th century and a foundational role in Vino Nobile di Montepulciano). As a 41st-generation winemaker living in the family palazzo right on Piazza Grande, Andrea’s passion and deep knowledge bring the wines to life in an intimate, unforgettable way. Savor their world-renowned Vino Nobile and other exceptional vintages in this truly privileged setting. Scenic lunch at Ristorante Romantico, followed by free time to explore Montepulciano’s medieval streets, Renaissance architecture, charming shops, and legendary gelato spots. Evening brings dinner at Ristorante Daria in the picturesque medieval village of Monticchiello. This intimate gem on the main street of this charming, tourist-light hill town offers warm hospitality, outstanding Tuscan cuisine, and a delightful, authentic atmosphere that perfectly captures the soul of the region. Accommodation: Hotel La Chiusa.

Day 3: September 27, 2027 – Truffle Hunting & Return to La Chiusa After breakfast, we head out with our longtime friend — the region’s top truffle hunter — for a truly magical truffle-hunting experience in the nearby forests. Kent and Allison have a special, longstanding friendship with this wonderful guide, who will lead us with his expertly trained dogs in search of these prized “black diamonds.” This time of the year, the truffles may be the highly sought-after white variety. The excitement of the hunt, the beauty of the Tuscan countryside, and the warm camaraderie make this one of the trip’s most memorable adventures. We return to La Chiusa to celebrate your finds with a delicious group lunch at the hotel, featuring dishes enhanced by the morning’s fresh truffles, paired with exceptional local wines and the estate’s own olive oil. Spend the afternoon at your leisure — nap by the pool, stroll the gardens, or simply savor the sweeping views. Dinner at Idyllium in enchanting Pienza. Perched on a historic terrace with views that will take your breath away—sweeping panoramas of the iconic Val d’Orcia UNESCO landscape, with its rolling hills, cypress trees, and golden light—this is one of the most spectacular settings in Tuscany. As the sun sets, the experience becomes even more magical, paired with masterful food and wine. Accommodation: Hotel La Chiusa.

Day 4: September 28, 2027 – E-Bike Adventure or Guided Walks Today offers two wonderful options, both starting and ending at La Chiusa under expert guidance—choose based on your energy and interests (both promise stunning scenery and memorable moments). E-Bike Group: Glide through the charming streets of Montefollonico and onto Tuscany’s legendary strade bianche—ancient white gravel roads dating back thousands of years. These timeless routes wind gracefully through vineyards, olive groves, and picturesque villages, offering an exhilarating yet accessible way to immerse yourself in the living landscape of Tuscany. Walkers Group: Enjoy a more leisurely and equally rewarding pace with leisurely strolls through Montefollonico’s enchanting lanes, followed by scenic low-traffic roads and nature trails bursting with panoramic views. Both groups reconvene for a delightful midway lunch. In the evening, gather at the vibrant Osteria Acquacheta in Montepulciano—famous for its open-kitchen grilling, lively atmosphere, and authentic Tuscan fare. Accommodation: Hotel La Chiusa.

Day 5: September 29, 2027 – Baracchi Winery & Cortona Following breakfast, visit Baracchi Winery, a distinguished 5th-generation estate. Tour the vineyards, enjoy an exclusive tasting, and savor an iconic lunch at their Michelin-starred restaurant. Continue to the captivating hilltop town of Cortona for an optional guided tour or free exploration of its historic streets, museums, and views. Stop for gelato at the beloved Dolce Vita before returning to La Chiusa. Cap the day with dinner at the on-site Ristorante La Chiusa—a historic estate with Etruscan roots, offering a magical, atmospheric dining experience with innovative yet traditional Tuscan cuisine. Accommodation: Hotel La Chiusa.

Day 6: September 30, 2027 – Cook in Tuscany & Cantine Innocenti A highlight day at Cook in Tuscany, one of Tuscany’s premier cooking schools located right on the La Chiusa estate. Led by local Tuscan women (the beloved “Nonnas”), you’ll dive into generational recipes using fresh garden ingredients. Learn to make handmade pici pasta, stuffed zucchini flowers, rich ragù, and more in a joyful, immersive kitchen experience filled with laughter, stories, and authentic techniques passed down through families. After the class, we’ll gather for a fun, festive group late lunch right on the estate, savoring the delicious dishes we created together—paired with La Chiusa wines and plenty of shared stories and laughter. Short walk to family-run Cantine Innocenti in Montefollonico for an intimate wine tasting—perfectly romantic and small-scale. Dinner at 13 Gobbi in Montefollonico’s peaceful medieval heart. Accommodation: Hotel La Chiusa.

Day 7: October 1, 2027 – Vintage Fiat Adventure & Private Olive Grove Dinner After breakfast, embark on a guest-favorite adventure: driving vintage Fiats through Tuscany’s scenic countryside, guided by experts. Wind along back roads with stops for photos and stories—pure joy on wheels. Return to La Chiusa for relaxation by the pool or in your suite. In the evening, enjoy a special private farewell dinner in the magical olive grove on the La Chiusa estate—surrounded by ancient trees, twinkling lights, and sweeping valley views. This intimate setting features exquisite Tuscan cuisine, exceptional local wines, and heartfelt toasts to new friendships and unforgettable memories. Accommodation: Hotel La Chiusa.

Day 8: October 2, 2027 – Departure Final La Chiusa breakfast before private transfer back to Florence.